Manager, Billing & Accounts Receivable

Own billing and collections for Enterprise and DSO accounts, including complex, contract-driven invoicing (multi-location rollups, tiered pricing, custom terms, milestone or usage-based fees).

Manage a smaller number of high-dollar, high-touch relationships, working directly with customer finance and procurement contacts to resolve disputes and negotiate payment plans where needed.

Partner with Legal and Sales on contract terms that affect billing and collectability (payment terms, invoicing triggers, true-ups, nonrefundable fee language) before deals close.

Serve as the point of escalation for at-risk Enterprise receivables, including past-due balances tied to contractual disputes.

Design and implement the systems, policies, and controls Pearl needs as it scales toward $100M+ ARR - this is a build role, not a maintain role.

Evaluate and implement billing/AR tooling and automation (in partnership with RevOps and Data) to reduce manual work and support both high-volume SMB and complex Enterprise billing in one coherent system.

Establish credit policies, write-off and bad debt procedures, and revenue recognition-adjacent controls in partnership with the Controller.

Build the billing/AR reporting Pearl does not yet have: aging, DSO, cash forecasting inputs, and collections effectiveness, for use in board and leadership reporting.

Partner with Sales and Customer Success to ensure pricing and sales initiatives - discounts, free months, promotional terms, contract concessions - are implemented correctly and consistently in billing systems, so what was sold matches what is invoiced.

Manage and grow the Billing/AR team, starting with one direct report today and scaling headcount as volume and complexity require.

Bring an AI-forward mindset to a function that is still largely manual across the industry: identify where AI and automation can replace manual dunning, reconciliation, and dispute triage work.

Use AI tools to accelerate collections outreach, aging analysis, and reporting rather than defaulting to spreadsheets and manual follow-up.

Partner with RevOps and Data to pilot AI-enabled billing and collections workflows, such as automated dispute categorization or payment risk scoring, as Pearl scales.

Experience in healthcare, dental, or another regulated vertical with multi-location or DSO-style customer structures.

Experience partnering with Legal on contract terms that affect billing and collectability.

Prior people management experience or a track record of being an early hire who later built and led a team.